Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

4. Alkanes and Cycloalkanes

Drawing Newman Projections

Organic Chemistry

4. Alkanes and Cycloalkanes

Drawing Newman Projections

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3:47 minutes

Problem 41

Textbook Question

Convert the following Newman projections to skeletal structures and name them.
a.
b.

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Examine the Newman projection carefully. Identify the front carbon (the circle) and the back carbon (the dot behind the circle). Note the substituents attached to each carbon and their relative positions (e.g., staggered or eclipsed).

Determine the connectivity of the substituents to the front and back carbons. Translate this information into a 2D skeletal structure by arranging the substituents around the carbons in the correct spatial orientation.

Draw the skeletal structure by representing the carbon chain as a zigzag line, with substituents branching off at the appropriate positions. Use wedges and dashes to indicate substituents that are coming out of or going into the plane of the paper, if necessary.

Verify the structure by ensuring that the connectivity and spatial arrangement of substituents in the skeletal structure match the Newman projection. Double-check for any stereochemical details, such as chirality centers, if present.

Name the compound according to IUPAC nomenclature rules. Identify the parent chain, number the carbons to give substituents the lowest possible numbers, and list substituents alphabetically in the name.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Newman Projections

Newman projections are a way to visualize the conformation of a molecule by looking straight down the bond connecting two carbon atoms. This representation helps in understanding the spatial arrangement of substituents around the bond, which is crucial for analyzing steric interactions and torsional strain in organic compounds.

Skeletal Structures

Skeletal structures, or line-angle formulas, are simplified representations of organic molecules where carbon atoms are represented by vertices and hydrogen atoms are often omitted for clarity. This format allows chemists to easily visualize the connectivity and functional groups within a molecule, making it essential for naming and understanding organic compounds.

Nomenclature of Organic Compounds

The nomenclature of organic compounds follows specific rules set by the International Union of Pure and Applied Chemistry (IUPAC). This system provides a standardized way to name compounds based on their structure, including the longest carbon chain, functional groups, and substituents, which is vital for clear communication in chemistry.

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Related Practice

Textbook Question

Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name.

(a)

(b)

Textbook Question

Draw a Newman projection, similar to Figure 3-25 down the C1—C6 bond in the equatorial conformation of methylcyclohexane. Show that the equatorial methyl group is also anti to C5. (Using your models will help.)

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Textbook Question

Draw Newman projections of the following molecules viewed from the direction of the blue arrows.

(b)

Textbook Question

Draw Newman projections of the following molecules viewed from the direction of the blue arrows.

(a)

Textbook Question

Draw all the staggered and eclipsed conformers that result from rotation about the C-2-C-3 bond of pentane.

Textbook Question

Using Newman projections, draw the most stable conformer for each of the following:

b. 3-methylhexane, viewed along the C-3----C-4 bond

Textbook Question

Using Newman projections, draw the most stable conformer for each of the following:

a. 3-methylpentane, viewed along the C-2---C-3 bond

Textbook Question

Draw a potential-energy diagram for rotation about the C-2---C-3 bond of pentane through 360°, starting with the least stable conformer.

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Convert the following Newman projections to skeletal structures and name them.a. b.

Key Concepts

Newman Projections

Skeletal Structures

Nomenclature of Organic Compounds

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Convert the following Newman projections to skeletal structures and name them.
a.
b.